ESPN Insider Warns Yankees’ Reward for Winning Could Be Red Sox Clash

Here’s your dose of playoff irony: even if the Yankees steamroll a cakewalk September schedule and finish with the second-best record in the American League, ESPN’s Buster Olney predicts they could still slide into the wild-card slot—facing the Red Sox right out of the gate.

“The Yankees have such a soft schedule in the final weeks that they wind up with the second-best record in the AL … but because Toronto holds on to win the division, New York is the No. 4 seed and faces Boston in the wild‑card round,” Olney predicted. 

That means even if New York beats up on the Orioles, White Sox, and other bottom-dwellers, it may not matter. The Blue Jays, by far the only real threat in the AL East, hang tough just enough to lock up the division, booting the Yankees into the wild-card well.

So, in the end, the Yankees get punished not for their effort, but for timing. They win their games, just when the rest of the division is busy struggling. And even so, they'll play in a minefield, likely a high-stakes Bronx showdown with Boston.

The Red Sox, who the Yankees are 2-8 against this season, are the last team they want to see in the postseason. The last time they met in the AL Wild Card, the Red Sox embarrassed Yankees ace Gerrit Cole and sent the Yankees packing. 

It’s a brutal slice of scheduling justice. 

The Yankees could end September with MVP-level numbers from Judge and Stanton, yet still draw Boston in a do-or-die matchup.